In the course of some studies establishing the absolute stereochemistry of aromatic metabolites (dihydro diols) the severe limitations associated with working with the small quantities of material available from enzymatic reactions became apparent. In order to overcome this problem we started a program on asymmetric synthesis. We have successfully demonstrated that substantial (several hundred mgs) amounts of optically active material (tetrahydro diols) suitable for determining the absolute stereochemistry of these compounds and other studies can be prepared. In the initial approach, cis and trans 3- phenyl 1,2-cyclohexane diols were obtained by reduction of alpha-acetoxy ketones with a chiral reducing agent (lithium aluminum hydride: darvon (1:2) complex). The resulting cis and trans diols were formed with enantiomer excesses of approximately 25-40%. The absolute stereochemistry of these compounds is currently under investigation. Suitable procedures for the preparation of alpha-acetoxy ketones in the phenanthrene series have been developed and the absolute stereochemistry of the resulting diols are under investigation.